The invention relates to an agent for dyeing (coloring) keratin-containing fibers, particularly human hair, comprising 1,2-dihydropyrimidinium derivatives in combination with reactive carbonyl compounds, the use of this combination in compositions for dyeing keratin-containing fibers, for color restoration or shading keratin-containing fibers that are already dyed, as well as a process for dyeing keratin-containing fibers, particularly human hair.
For dyeing keratin-containing fibers, generally either substantive dyestuffs or oxidation dyestuffs are used, the latter resulting from oxidative coupling of one or more developer components with each other or with one or more coupler components. Coupler and developer components are also referred to as oxidation dyestuff precursors.
Usually, primary aromatic amines with a further free or substituted hydroxyl or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives as well as 2,4,5,6-tetraminopyrimidine and its derivatives are employed as developer components.
Specific representatives are for example p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraminopyrimidine, p-aminophenol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)ethanol, 2-(2,5-diaminophenoxy)ethanol, 1-phenyl-3-carboxyamido-4-aminopyrazol-5-one, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
Generally, m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives. Suitable coupler substances are particularly α-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethylether, m-phenylenediamine, 2,4-diaminophenoxyethanol, 2-amino-4-(2-hydroxyethylamino)anisole (Lehmann's Blue), 1-phenyl-3-methylpyrazol-5-one, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 3-amino-6-methoxy-2-methylaminopyridine and 3,5-diamino-2,6-dimethoxypyridine are employed as coupler components.
With respect to other customary dyestuff components, reference is expressly made to the series “Dermatology”, edited by Ch. Culnan, H. Maibach, publisher Marcel Dekker Inc., New York, Basel, 1986, vol. 7, Ch. Zviak, The Science of Hair Care, ch. 7, pages 248–250 (substantive dyestuffs), and ch. 8, pages 264–267 (oxidation dyestuffs) and the “European Inventory of Cosmetic Raw Materials”, 1996, published by the European Commission, obtainable as a floppy disk from the Bundesverband der deutschen Industrie-und Handelsunternehmen für Arzneimittel, Reformwaren und Körperpflegemittel e.V., Mannheim.
Although intense colorations with good fastness properties can be obtained with oxidation dyestuffs, the development of the color generally occurs however, under the influence of oxidizing agents such as e.g. H2O2, which in some cases can result in damage to the fibers. The preparation of oxidation hair colorations in the reddish range with satisfactory fastness properties still proves to be problematic, particularly for very good wash fastness and rubbing fastness. Furthermore, some oxidation dyestuff precursors or particular mixtures of oxidation dyestuff precursors can sometimes produce a sensitizing effect on persons with sensitive skin. Substantive dyestuffs are applied under milder conditions but have the disadvantage that the colorations often suffer from inadequate fastness properties.
Colorants comprising 1,2-dihydropyrimidinium derivatives, together with their use for dyeing keratin-containing fibers or for color restoration or shading keratin-containing fibers that have already been dyed, are so far unknown.
Reactions of pyrimidones as methylene bases are described in the publication of H. Baumann et al., Liebigs Ann. Chem., 1968, 717, 124–136. A hair colorant comprising 1,2-dihydropyrimidinium derivatives, or the use of the disclosed hemicyanines for dyeing keratin-containing fibers is not suggested.
In the German patent application DE-A1-2047431, cationic methine dyestuffs are described for the coloration of anionically modified fibers such as acid modified polyesters or acrylonitrile polymers. For the synthesis of cationic methine dyestuffs, 3,4-dihydro-3-methyl-4-methylenequinazol-2-one and 1,3,6-trimethyl-4-methylenepyrimidine-2-one inter alia are used as well as imperatively terephthalaldehyde.
In the German patent application DE-A1-2165913, a process for the manufacture of bleached images by using light-sensitive dyestuffs is proposed. The claimed light-sensitive dyestuffs belong to the class of pyrimidone or thiopyrimidone dyestuffs.
The object of the present invention is to provide colorants for keratin-containing fibers, particularly human hair, which with respect to depth of color, gray coverage and fastness properties such as for example light-, rubbing- and wash fastness as well as perspiration fastness and cold-waving fastness, are qualitatively at least equal, particularly in the reddish range, to typical oxidation hair colorants, without however being necessarily dependent on oxidizing agents such as for example H2O2. Moreover, the dyes must not possess any, or only a very low degree of sensitization.